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Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

3.1K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
3.1K
Ziegler–Natta Chain-Growth Polymerization: Overview01:17

Ziegler–Natta Chain-Growth Polymerization: Overview

3.5K
Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
3.5K
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

2.0K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
2.0K
Radical Chain-Growth Polymerization: Overview01:10

Radical Chain-Growth Polymerization: Overview

2.7K
Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
2.7K
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN101:14

Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1

2.2K
Treating arylamines with nitrous acid gives aryldiazonium salts that are effective substrates in nucleophilic aromatic substitution reactions. The diazonio group in these salts can be easily displaced by different nucleophiles, yielding a wide variety of substituted benzenes. The leaving group departs as nitrogen gas, and this easy elimination is the driving force for the substitution reaction.
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
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Green and Sustainable Chemistry Approaches on Azide-Based Click Reactions in Polymer Science.

Hatice Mutlu1,2,3, Bercis Pektas1, C Remzi Becer4

  • 1Institut de Science des Matériaux de Mulhouse, UMR 7361 CNRS/Université de Haute Alsace, Mulhouse, France.

Macromolecular Rapid Communications
|August 6, 2025
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Summary

Click Chemistry, specifically the azide-alkyne cycloaddition (AAC) reaction, offers green and sustainable polymer synthesis. This review highlights challenges and solutions for optimizing AAC in polymer chemistry for enhanced environmental compatibility.

Keywords:
azide‐alkyne cycloadditionclick chemistryclick polymerizationcopper‐catalysed azide‐alkyne cycloadditionmetal‐free click chemistrysustainable chemistry

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Area of Science:

  • Polymer Chemistry
  • Green Chemistry
  • Organic Synthesis

Background:

  • Click Chemistry, particularly azide-alkyne cycloaddition (AAC), has transformed polymer synthesis.
  • AAC reactions exhibit high regioselectivity, mild conditions, and versatility, aligning with Green Chemistry principles.
  • The integration of AAC with Green Chemistry ideals in polymer chemistry requires further emphasis.

Purpose of the Study:

  • To evaluate the current limitations of AAC in polymer chemistry concerning sustainability.
  • To explore innovative solutions for greener AAC reactions in polymer synthesis.
  • To provide a roadmap for optimizing AAC for sustainable materials design.

Main Methods:

  • Review of current literature on AAC reactions in polymer chemistry.
  • Analysis of limitations, including hazardous reagents and non-renewable resources.
  • Exploration of greener catalysts, solvent-free systems, and renewable feedstocks.
  • Comparison of different activation methods (thermal, catalytic, metal-free, strain-promoted) for sustainability.

Main Results:

  • Identified challenges in AAC, such as hazardous azide use and reliance on petrochemicals.
  • Highlighted innovative solutions like eco-friendly catalysts and renewable starting materials.
  • Compared various activation methods, assessing their sustainability trade-offs.
  • Showcased practical applications of AAC in designing functional polymers.

Conclusions:

  • AAC is a powerful tool for sustainable polymer synthesis but faces environmental challenges.
  • Further research is needed to develop greener catalysts, solvents, and feedstocks for AAC.
  • Optimizing AAC for sustainability is crucial for advancing functional polymer design without compromising efficiency.